Synthesis of 6, 6-pentamethylene-2-aminosuberic acid. A key intermediate in the synthesis of dicarba analogs of vasopressin antagonists

JF Callahan, KA Newlander, HG Bryan…

Index: Callahan, James F.; Newlander, Kenneth A.; Bryan, Heidemarie G.; Huffman, William F.; Moore, Michael L.; Yim, Nelson C. F. Journal of Organic Chemistry, 1988 , vol. 53, # 7 p. 1527 - 1530

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Citation Number: 6

Abstract

Two complementary syntheses of the unnatural amino acid, 6, 6-cyclopentamethylene-2- aminosuberic acid, Pas (2) are described. The first, starting from methyl cyclohexanecarboxylate (a), yields in ten steps racemic Boc-Pas (OBz1)-OH (3) which is suitably protected for solid phase peptide synthesis. The second method involves the stereospecific synthesis of optically pure Boc-Pas (OBz1)-OH (3L) utilizing the ...